Water → 6-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl ester

HRID 1947481Notes

Reaction equation

F[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][O:13][C:14](=[O:17])[CH2:15][SH:16].CCN(CC)CC.O>CS(C)=O>[CH3:12][O:13][C:14]([C:15]1[S:16][C:2]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=2[CH:4]=1)=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-fluoro-4-methoxy-benzaldehyde (4.0 g, 26 mmol) in DMSO (200 mL) was added mercapto-acetic acid methyl ester (3.6 mL, 3.9 g, 39 mmol) and Et3N (10.8 mL, 7.8 g, 78 mmol) and the reaction mixture was heated (80° C., 12 h). The reaction mixture was cooled (rt) and treated with H2O (100 mL). The suspension was filtered to afford the title compound as a yellow solid (4.1 g, 71%). MS (ESI): mass calcd. for C11H10O3S, 222.0; m/z found, 223.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.97 (d, J=0.6, 1H), 7.74 (d, J=8.8, 1H), 7.28 (d, J=2.3, 1H), 7.02 (dt, J=8.7, 4.3, 1H), 3.92 (s, 3H), 3.89 (s, 3H).

Workup

temperatureThe reaction mixture was cooled (rt)
filtrationThe suspension was filtered

Sources & evidence

ORD record: ord-f83a282f086d42fb98781d2008f1259c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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